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Hoffman AJ, Nichols DE. 
“Synthesis and LSD-like discriminative stimulus properties in a series of N6-alkyl norlysergic acid N,N-diethylamide derivatives”. 
J Med Chem. 1985 Sep 17;28(9):1252-5.
A convenient method for the synthesis of N6-alkyl norlysergic acid N,N-diethylamide derivatives was developed. A series of these compounds was synthesized and tested for substitution in the two-lever drug discrimination assay, in rats trained to discriminate injections of d-LSD tartrate 185.5 nmol/kg, ip from saline. A dose-response curve for each of the compounds in the series was generated. Structure-activity relationships were developed, based on comparison of the estimated ED50 values from these curves. Of the compounds that substituted for LSD, the N6-ethyl and -allyl were approximately 2-3 times more potent than LSD itself. The N6-propyl was equipotent to LSD, while the isopropyl derivative was half as active. The n-butyl compound was 1 order of magnitude less potent than LSD, suggesting a similarity to the SAR of certain serotonin and dopamine agonists. By contrast, no generalization occurred to norlysergic acid N,N-diethylamide and the N6-2-phenethyl derivative.
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